Molecular Study of Capsaicin in Aqueous and Hydrophobic Environments

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dc.contributor.authorLambert, Joseph Walteren
dc.contributor.committeechairSum, Amadeu K.en
dc.contributor.committeememberMarand, Evaen
dc.contributor.committeememberBevan, David R.en
dc.contributor.departmentChemical Engineeringen
dc.date.accessioned2014-03-14T20:39:44Zen
dc.date.adate2006-08-22en
dc.date.available2014-03-14T20:39:44Zen
dc.date.issued2006-06-08en
dc.date.rdate2006-08-22en
dc.date.sdate2006-06-09en
dc.description.abstractAnyone who has eaten spicy foods has experienced the adverse effects of capsaicin, the pungent chemical found in hot chili that causes a burning sensation. The specific action of capsaicin occurs by the activation of receptors in sensory neurons. This thesis investigates the interaction of capsaicin with model cell membranes representing the structure of neurons. In particular, we are interested in the changes induced by capsaicin to the structure and dynamics of membranes. Molecular dynamics simulations are used to study the molecular interactions. The first part of this study evaluates different molecular representations for capsaicin in an 1-octanol/water system. This inhomogeneous system is commonly used to determine the partition of compounds between hydrophilic and hydrophobic environments, as that found in biological membranes. The results of these simulations validate the OPLS united-atom force field as a reasonable molecular representation of capsaicin, as it describes the behavior of capsaicin both quantitatively and qualitatively in 1-octanol/water mixtures. In the second part, simulations are performed for capsaicin and model cell membranes consisting of dipalmitoylphosphatidylcholine and dipalmitoylphosphatidylethanolamine, two of the most commonly found lipids. Simulations investigated capsaicin in the aqueous and lipid phases. The results provide insight into the changes to the bilayers caused by capsaicin. Bilayers containing dipalmitoylphosphatidylethanolamine showed lower permeabilities to capsaicin than those composed of pure dipalmitoylphosphatidylcholine. Temperature is found to be an important factor in the permeability of capsaicin in the bilayer. Capsaicin in the bilayer concentrated in a region beneath the lipid/water interface, in which favorable hydrophilic and lipophilic interactions occur. The structure of the bilayer is not significantly changed at the concentrations of capsaicin considered. One important result from the simulations indicates that the interfacial density decreases with increasing capsaicin concentration in the bilayer, supporting the experimental observations of increased permeability in bilayers exposed to capsaicin.en
dc.description.degreeMaster of Scienceen
dc.identifier.otheretd-06092006-132651en
dc.identifier.sourceurlhttp://scholar.lib.vt.edu/theses/available/etd-06092006-132651/en
dc.identifier.urihttp://hdl.handle.net/10919/33495en
dc.publisherVirginia Techen
dc.relation.haspartthesis.pdfen
dc.rightsIn Copyrighten
dc.rights.urihttp://rightsstatements.org/vocab/InC/1.0/en
dc.subjectOctanol-wateren
dc.subjectLipid Bilayeren
dc.subjectSimulationsen
dc.subjectMolecular Dynamicsen
dc.subjectCapsaicinen
dc.titleMolecular Study of Capsaicin in Aqueous and Hydrophobic Environmentsen
dc.typeThesisen
thesis.degree.disciplineChemical Engineeringen
thesis.degree.grantorVirginia Polytechnic Institute and State Universityen
thesis.degree.levelmastersen
thesis.degree.nameMaster of Scienceen

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